Villas, the island on your own terms

A private villa with its own pool and garden inside The Cliff Bay’s grounds — total seclusion plus the hotel’s machinery on call: room service, the spa, the ocean swimming platform, two-Michelin-star dinners a short walk away. For a family or two couples who have outgrown hotel rooms but not hotel service, nothing else in Funchal does this combination. Priced accordingly.

The architecture project of Funchal’s old town: a sustainable rebuild in reclaimed stone and timber on Rua do Lazareto that has run in Architectural Digest and Condé Nast Traveller, with four en-suite bedrooms and a rooftop garden whose infinity pool looks across the harbour. It is a design object you get to live in for a week — priced like one, too: you will want six or eight of you to justify it. Book it for the house itself; the city happens to be attached.

Four hundred square metres of walled seafront garden in the middle of Funchal — banana trees, a herb patch, a private pool and the Atlantic just over the wall. The house itself is a simple two-bedroom; you are paying for land and position, ten minutes on foot from the old town. For a family that wants the city without a hotel, it is close to unrepeatable.

A townhouse in the Zona Velha with the sea at the end of the street — restored old-town Funchal on the outside, contemporary comfort within, and the city’s best restaurants, the cable car and the Barreirinha lido all inside a few hundred metres. It sleeps a family, and you will not touch the car. The old town stays lively after dark; that is either the feature or the bug.

A contemporary house above the Barreirinha lido at the eastern edge of the old town — terraces stacked toward the sea, Funchal’s best swimming spot below, and the restaurants of Rua de Santa Maria five minutes on foot. The location earns the rate: sea-facing, walkable, residential-quiet at night. Right for a couple or a small family; the hire car will sit parked for days.

Townhouses restored by Bordal, the Madeira embroidery house that still hand-stitches in its Funchal factory — each one furnished with the family’s linens and a deliberate, unforced Madeiran-ness that designer rentals imitate badly. Central, sensibly priced, and connected to a living craft tradition rather than a property manager. These are traditional houses, not luxury ones: expect character and stairs, not a concierge.

Six traditional houses scattered through gardens and orchards in Ponta do Pargo, Madeira’s quiet far-western parish — sea views from the lawn, a shared pool, and the kind of silence the south coast lost years ago. Houses sleep two to eight, so it works for families and small groups. Funchal is the better part of an hour away; dinner means cooking or the village. That is the deal.

Restored fishermen’s houses at Calhau da Lapa, a hamlet on the water below Campanário that no road reaches — you arrive by summer water taxi from Ribeira Brava or on foot down roughly seven hundred stone steps. Once there: the sea, the cliff, a terrace, and nothing else. Two simply fitted houses. The most radical stay on this list; pack light and check the boat schedule.

A three-bedroom villa above the sea in Ponta Delgada on the north coast, with a private pool aimed at the Atlantic and the village — restaurants, a mini-market, a natural sea-swimming complex — a few minutes’ walk below. The north is green, dramatic and wetter than the south; in exchange you get this coastline nearly to yourself, even in August.

One of a handful of houses on a 25,000-square-metre vineyard estate in São Vicente, where terraces of tinta negra and verdelho run up into the laurissilva forest. A shared pool, gardens with a 250-year-old oak, and proper darkness at night. The house takes its name from the rarest grape in the Madeira cellar — fitting for a stay this far off the circuit.